Silver halide color photographic material

Abstract

There is disclosed a silver halide color photographic material which comprises in a blue-sensitive silver halide emulsion layer acylacetamide yellow dye-forming couplers represented by the following formula (I) and in a red-sensitive silver halide emulsion layer cyan dye-forming couplers represented by the following formula (II) or (III): ##STR1## wherein R 1 represents a monovalent group, Q represents a group of non-metallic atoms required to form together with the C a substituted or unsubstituted 3- to 5-membered cyclic hydrocarbon group or a substituted or unsubstituted 3- to 5-membered heterocyclic group having therein at least one heteroatom selected from a group consisting of N, O, S, and P, and Y R represents a residue remaining after removing the acyl group from the acylacetamide yellow dye-forming coupler, provided that R 1 is not a hydrogen atom and does not bond to Q to form a ring, ##STR2## wherein R 1 represents --CONR 4 R 5 , --SO 2 NR 4 R 5 , --NHCOR 4 , --NHCOOR 6 , --NHSO 2 R 6 , --NHCONR 4 R 5 , or --NHSO 2 NR 4 R 5 ; R 2 represents a group substitutable on a naphthalene ring; k is an integer of 0 to 3; R 3 represents a substituent, X 1 represents a hydrogen atom or a coupling split-off group; R 4 and R 5 , which may be the same or different, each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R 6 represents an alkyl group, an aryl group, or a heterocyclic group; when k is 2 or more, the R 2 groups may be the same or different and may bond together to form a ring; and the compound may form a dimer or higher polymer formed by bonding through a divalent group or higher polyvalent group at R 1 , R 2 , R 3 , or X 1 , ##STR3## wherein R 21 represents an alkyl group, an aryl group, or a heterocyclic group, R 22 represents an aryl group, and Z 1 represents a hydrogen atom or a coupling split-off group.

What we claim is: 
     
       1. A silver halide color photographic material having at least one red-sensitive silver halide emulsion layer, at least one green-sensitive silver halide emulsion layer, and at least one blue-sensitive silver halide emulsion layer on a support, which comprises, in at least one of said blue-sensitive silver halide emulsion layer, at least one coupler selected from an acylacetamide yellow dye-forming coupler represented by the following formula (I) and, in at least one of said red-sensitive silver halide emulsion layer, at least one coupler selected from the group consisting of cyan dye-forming couplers represented by the following formula (II) or (III): ##STR125## wherein R 1  represents a monovalent group, Q represents a group of non-metallic atoms required to form together with the C a substituted or unsubstituted 3- to 5-membered cyclic hydrocarbon group or a substituted or unsubstituted 3- to 5-membered heterocyclic group having therein at least one heteroatom selected from a group consisting of N, O, S, and P, and Y R  represents a residue remaining after removing the acyl group ##STR126## from the acylacetamide yellow dye-forming coupler represented by formula (I), provided that R 1  is not a hydrogen atom and does not bond to Q to form a ring, ##STR127## wherein R 1  represents --CONR 4  R 5 , --SO 2  NR 4  R 5 , --NHCOR 4 , --NHCOOR 6 , --NHSO 2  R 6 , --NHCONR 4  R 5 , or --NHSO 2  NR 4  R 5  ; R 2  represents a group capable of substitution on a naphthalene ring; k is an integer of 0 to 3; R 3  represents a substituent, X 1  represents a hydrogen atom or a group capable of being released upon a coupling reaction thereof with the oxidized product of an aromatic primary amine developing agent; R 4  and R 5 , which may be the same or different, each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R 6  represents an alkyl group, an aryl group, or a heterocyclic group; when k is 2 or more, the R 2  groups may be the same or different and may bond together to form a ring; and the compound may form a dimer or higher polymer formed by bonding through a divalent group or higher polyvalent group at R 1 , R 2 , R 3 , or X 1 , ##STR128## wherein R 21  represents an alkyl group, an aryl group, or a heterocyclic group, R 22  represents an aryl group, and Z 1  represents a hydrogen atom or a group capable of being released upon a coupling reaction thereof with the oxidized product of an aromatic primary amine developing agent. 
     
     
       2. The silver halide color photographic material as claimed in claim 1, wherein the red-sensitive silver halide emulsion layer contains the cyan dye-forming coupler represented by formula (II). 
     
     
       3. The silver halide color photographic material as claimed in claim 1, wherein the red-sensitive silver halide emulsion layer contains the cyan dye-forming coupler represented by formula (III). 
     
     
       4. The silver halide color photographic material as claimed in claim 1, wherein the acetylacetamide yellow dye-forming coupler is represented by the following formula (Y): ##STR129## wherein R 1  represents a monovalent substituent other than hydrogen; Q represents a group of non-metallic atoms required to form together with the C a substituted or unsubstituted 3- to 5-membered cyclic hydrocarbon group or a substituted or unsubstituted 3- to 5-membered heterocyclic group having in the group at least one heteroatom selected from a group consisting of N, O, S, and P; R 2  represents a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, or an amino group, R 3  represents a group capable of substitution onto a benzene ring, X represents a group capable of being released upon a coupling reaction thereof with the oxidized product of an aromatic primary amine developing agent, l is an integer of 0 to 4, and when l is 2 or more, the R 3  groups may be the same or different. 
     
     
       5. The silver halide color photographic material as claimed in claim 1, wherein R 1  in formula (I) is selected from a group consisting of alkyl groups having a total C-number of 1 to 5. 
     
     
       6. The silver halide color photographic material as claimed in claim 1, wherein R 1  in formula (I) is a methyl group, an ethyl group, or an n-propyl group. 
     
     
       7. The silver halide color photographic material as claimed in claim 6, wherein R 1  in formula (I) is a methyl group. 
     
     
       8. The silver halide color photographic material as claimed in claim 1, wherein the ring formed by Q together with the C in formula (I) is a substituted or unsubstituted 3-, 4-, or 5-membered cyclic hydrocarbon group. 
     
     
       9. The silver halide color photographic material as claimed in claim 8, wherein the ring formed by Q together with the C in formula (I) is a substituted or unsubstituted 3-membered cyclic hydrocarbon group. 
     
     
       10. The silver halide color photographic material as claimed in claim 4, wherein X in formula (Y) represents a heterocyclic group bonded to the coupling active site through the nitrogen atom or an aryloxy group. 
     
     
       11. The silver halide color photographic material as claimed in claim 4, wherein R 3  in formula (Y) represents a halogen atom, an alkoxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonamido group, a sulfonamido group, a carbamoyl group, or a sulfamoyl group. 
     
     
       12. The silver halide color photographic material claimed in claim 1, wherein the acylacetamide yellow dye-forming coupler represented by formula (I) is present in an amount of 1×10 -3  to 1 mol per mol of the silver halide in the yellow coupler containing layer. 
     
     
       13. The silver halide color photographic material as claimed in claim 1, wherein the acylacetamide yellow dye-forming coupler represented by formula (I) is contained in a blue-sensitive silver halide emulsion layer and the silver amount of which is 0.1 to 10 g/m 2  of the silver halide color photographic material. 
     
     
       14. The silver halide color photographic material as claimed in claim 1, wherein the amount of the cyan coupler represented by formula (II) or (III) to be added is 1×10 -3  mol to 1 mol, per mol of silver halide in the layer where the coupler is present 
     
     
       15. A method for forming a color image, comprising, subjecting the silver halide color photographic material as claimed in claim 1, after its imagewise exposure, to color development followed by desilvering. 
     
     
       16. The method for forming a color image as claimed in claim 15, wherein iron (III) ethylenediaminetetraacetate or iron (III) 1,3-diaminopropanetetraacetate is a bleaching agent for the desilvering step. 
     
     
       17. The silver halide color photographic material as claimed in claim 4, wherein R 3  in formula (Y) is selected from the group consisting of a halogen atom, an alkyl group having C-number of 1 to 30, an aryl group having C-number of 6 to 30, an alkoxy group having C-number of 1 to 30, an aryloxy group having C-number of 6 to 30, an alkoxycarbonyl group having C-number of 2 to 30, an aryloxycarbonyl group having C-number of 7 to 30, a carbonamido group having C-number of 1 to 30, a sulfonamide group having C-number of 1 to 30, a carbamoyl group having C-number of 1 to 30, a sulfamoyl group having C-number of 0 to 30, an alkylsulfonyl group having C-number of 1 to 30, an alkylsulfonyl group having a C-number of 6 to 30, a ureido group having C-number of 1 to 30, a sulfamoylamino group having C-number of 0 to 30, an alkoxycarbonylamino group having C-number of 2 to 30, an alkoxysulfonyl group having C-number of 1 to 30, a nitro group, a heterocyclic group having C-number of 1 to 30, a cyano group, an acyl group having C-number of 1 to 30, an acyloxy group having C-number of 2 to 30, an alkylsulfonyloxy group having C-number of 1 to 30, and an arylsulfonyloxy group having C-number of 6 to 30. 
     
     
       18. The silver halide color photographic material as claimed in claim 4, wherein X in formula (Y) is selected from the group consisting of succinimido, maleinimido, phthalimido, diglycolimido, pyrrole, pyrazole, imidazole, 1,2,4-triazole, tetrazole, indole, indazole, benzimidazole, benzotriazole, imidazolidin-2,4-dione, oxazolidine-2,4-dione, thiazolidine-2,4-dione, imidazolidine-2-one, oxazolidine-2-one, thiazolidine-2-one, benzimidazolidine-2-one, benzoxazolidine-2-one, benzothiazolidine-2-one, 2-pyrroline-5-one, 2-imidazolidine-5-one, indoline-2,3-dione, 2,6-dioxypurine, parabanic acid, 1,2,4-traizolidine-3,5-dione, 2-pyridone, 4-pyridone, 2-pyrimidone, 6-pyridazone-2-pyrazone, 2-amino-1,3,4-thiazolidine, and 2-imino-1,3,4-thiazolidine-4-one. 
     
     
       19. The silver halide color photographic material as claimed in claim 4, wherein R 2  in formula (Y) represents a chlorine atom, a fluorine atom, an alkyl group having C-number of 1 to 6, an alkoxy group having C-number of 1 to 8, or an aryloxy group having C-number of 6 to 24. 
     
     
       20. The silver halide color photographic material as claimed in claim 4, wherein R 3  in formula (Y) represents a halogen atom, an alkoxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonamido group, a sulfonamido group, a carbamoyl group, or a sulfamoyl group. 
     
     
       21. The silver halide color photographic material as claimed in claim 4, wherein X is a group represented by the following formula (Y-1), (Y-2) or (Y-3): ##STR130## wherein Z represents --O--CR 4  (R 5 )--, --S--CR 4  (R 5 )--, --NR 6  --CR 4  (R 5 )--, --NR 6  --NR 7  --, --NR 6  --C(O)--, CR 4  (R 5 )--CR 8  (R 9 )-- or --CR 10  ═CR 11  --, wherein R 4 , R 5 , R 8 , and R 9 , same or different, each represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, or an amino group; R 6  and R 7  each represent a hydrogen atom, an alkyl group, an aryl group, an alkylsulfonyl group, an arylsulfonyl group, or an alkoxycarbonyl group; R 10  and R 11  each represent a hydrogen atom, an alkyl group, or an aryl group, or R 10  and R 11  may bond together to form a benzene ring; and R 4  and R 5 , R 5  and R 6 , R 6  and R 7 , or R 4  and R 8  may bond together to form a 3- to 8-membered heterocyclic or hydrocarbon ring, which may be substituted; ##STR131## wherein at least one of R 12  and R 13  is selected from the group consisting of a halogen atom, a cyano group, a nitro group, trifluoromethyl, a carboxyl group, an alkoxycarbonyl group, a carbonamido group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, and an acyl group and the other may be a hydrogen atom, an alkyl group, or an alkoxy group; R 14  has the same meaning as that of R 12  or R 13 , and m is an integer of 0 to 2; ##STR132## wherein W represents a group of non-metallic atoms required to form together with N a pyrrole ring, a pyrazole ring, an imidazole ring or a triazole ring.   
     
     
       22. The silver halide color photographic material as claimed in claim 4, wherein the ring formed by Q together with the C is selected from the group consisting of a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclopropene ring, a cyclobutene ring, a cyclopentene ring, an oxetane ring, an oxolane ring, a 1,3-dioxolane ring, a thiethane ring, a thiolane ring, and a pyrrolidine ring. 
     
     
       23. The silver halide color photographic material as claimed in claim 4, wherein R 1  is a halogen atom, a cyano group, an unsubstituted or a substituted alkyl group, an unsubstituted or a substituted alkoxy group, an unsubstituted or a substituted aryl group, an unsubstituted or a substituted aryloxy group, cyclopentyl, cyclohexyl, allyl, 3-cyclohexenyl, oleyl, benzyl, trifluoromethyl, hydroxymethyl-methoxyethyl, ethoxycarbonylmethyl or phenoxyethyl, wherein the substituents are selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, a nitro group, an amino group, a carbonamido group, a sulfonamido group, an acyl group, and combinations thereof or the aryl group is substituted by a substituent selected from the group consisting of phenyl, 1-naphthyl, p-tolyl, o-tolyl, p-chlorophenyl, 4-methoxyphenyl, 8-quinolyl, 4-hexadecyloxyphenyl, pentafluorophenyl, p-hydroxyphenyl, p-cyanophenyl, 3-pentadecylphenyl, 2,4-di-t-pentylphenyl, p-methanesulfonamideophenyl, and 3,4-dichlorophenyl; Q represents a group of non-metallic atoms which forms together with the carbon atom a substituted or unsubstituted 3 to 5 membered cyclic hydrocarbon ring having a total carbon number of 3 to 30, or a substituted or unsubstituted 3 to 5 member heterocyclic group having a total C-number of 2 to 30 and having in the group at least one heteroatom selected from the group consisting of N, O, S and P;   R 2  represents a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, an amino group, cyclopentyl, cyclohexyl, allyl, 3-cyclohexenyl, oleyl, benzyl, trifluoromethyl, hydroxymethyl-methoxyethyl, ethoxycarbonylmethyl or phenoxyethyl; wherein the substituents are selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an aryloxy group and combinations thereof;   R 3  is a halogen atom, an unsubstituted or substituted alkyl group, cyclopentyl, cyclohexyl, allyl, 3-cyclohexenyl, oleyl, benzyl, trifluoromethyl, hydroxymethylmethoxyethyl, ethoxycarbonylmethyl, phenoxyethyl, an unsubstituted or substituted aryl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxycarbonyl group, an unsubstituted or substituted carbonamido group, an unsubstituted or substituted sulfonamido group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted sulfamoyl group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted ureido group, an unsubstituted or substituted sulfamoylamino group, an unsubstituted or substituted alkoxycarbonylamino group, an unsubstituted or substituted alkoxysulfonyl group, a nitro group, an unsubstituted or substituted heterocyclic group, a cyano group, an unsubstituted or substituted acyl group, an unsubstituted or substituted acyloxy group, an unsubstituted or substituted alkylsulfonyloxy group, or an unsubstituted or substituted arylsulfonyloxy group, wherein the substituents are selected from the group consisting of a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, a heterocyclic thio group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, a carbonamido group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonylamino group, a sulfamoylamino group, a ureido group, a cyano group, a nitro group, an acyloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyloxy group, an arylsulfonyloxy group and combinations thereof;   X represents a hydrogen atom or a group capable of being released upon a coupling reaction thereof with an oxidized product of an aromatic primary amine developing agent; l is an integer of 0 to 4, and when l is 2 or more, the R 3  groups may be the same or different.   
     
     
       24. The silver halide color photographic material as claimed in claim 4, wherein R 1  is a halogen atom, a cyano group, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, cyclopentyl, cyclohexyl, allyl, 3-cyclohexenyl, oleyl, benzyl, trifluoromethyl, hydroxymethymethoxyethyl, ethoxycarbonylmethyl or phenoxyethyl. 
     
     
       25. The silver halide color photographic material as claimed in claim 4, wherein the ##STR133## group formed by R 1  and Q with C is selected from the group consisting of: ##STR134## 
     
     
       26. The silver halide color photographic material as claimed in claim 4, wherein X represents a 3 to 8 heteroyclic ring containing group that contains at least one heteroatom selected from the group consisting of O, N, S, P, Se and Te and is bonded to the coupling site through a nitrogen atom or an aryloxy group and contains from 2 to 36 carbon atoms and is capable of being released upon a coupling reaction thereof with an oxidizing product of an aromatic primary amine developing agent. 
     
     
       27. The silver halide color photographic material as claimed in claim 4, wherein X is selected from the group consisting of: ##STR135## 
     
     
       28. The silver halide color photographic material as claimed in claim 23, wherein the substituents are selected from the group consisting of a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, a sulfo group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an amino group, a carbonamido group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, an ureido group, an alkoxycarbonylamino group, and a sulfamoylamino group. 
     
     
       29. The silver halide color photographic material as claimed in claim 4, wherein R 2  is selected from the group consisting of: ##STR136## 
     
     
       30. The silver halide color photographic material as claimed in claim 4, wherein R 2  represents a halogen atom, an alkoxy group that may be substituted and has a total of 1 to 30 carbon atoms, an aryloxy group that may be substituted and has a total of 6 to 30 carbon atoms, an alkyl group that may be substituted and has a total of 1 to 30 carbon atoms or an amino group that may be substituted and has a total of 0 to 30 carbon atoms, wherein the substituents of the alkoxy group, aryloxy group, alkyl group and amino group is selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group and an aryloxy group. 
     
     
       31. The silver halide color photographic material as claimed in claim 4, wherein R 3  is selected from the group consisting of: ##STR137## 
     
     
       32. The silver halide color photographic material as claimed in claim 4, wherein l is an integer of 1 or 2 and the position of the substitution of R 3  is the meta-position or para-position relative to ##STR138## 
     
     
       33. The silver halide color photographic material as claimed in claim 21, wherein the total number of carbon atoms of the heterocyclic group represented by formula (Y-1) is 2 to 30. 
     
     
       34. The silver halide color photographic material as claimed in claim 21, wherein the total number of carbon atoms of the heterocyclic group represented by formula (Y-2) is 6 to 30. 
     
     
       35. The silver halide color photographic material as claimed in claim 21, wherein the total number of carbon atoms of the heterocyclic group represented by formula (Y-3) is 2 to 30. 
     
     
       36. The silver halide color photographic material as claimed in claim 4, wherein X represents a substituted or unsubstituted heterocyclic group selected from succinimido, maleinimido, phthalimido, diglycolimido, pyrrole, pyrazole, imidazole, 1,2,4-triazole, tetrazole, indole, indazole, benzimidazole, benzotriazole, imidazolidine-2,4-dione, oxazolidine-2,4-dione, thiazolidine-2,4-dione imidazolidine-2-one, oxazolidine-2-one, thiazolidine-2-one, benzimidazoline-2-one, benzoxazolidine-2-one, benzothiazoline-2-one, 2-pyrroline-5-one, 2-imidazoline-5-one, indoline-2,3-dione, 2,6-dioxypurine, parabanic acid, 1,2,4-traizolidine-3,5-dione, 2-pyridone, 4-pyridone, 2-pyrimidone, 6-pyridazone-2-pyrazone, 2-amino-1,3,4-thiazolidine, and 2-imino-1,3,4-thiazolidine-4-one. 
     
     
       37. The silver halide color photographic material as claimed in claim 1, wherein R 1  in Formula (II) is selected from the group consisting of: ##STR139## 
     
     
       38. The silver halide color photographic material as claimed in claim 1, wherein R 2  in Formula (II) is selected from the group consisting of: ##STR140## 
     
     
       39. The silver halide color photographic material as claimed in claim 1, wherein R 3  NH-- in Formula (II) is selected from the group consisting of: ##STR141## 
     
     
       40. The silver halide color photographic material as claimed in claim 1, wherein X 1  in Formula (II) is selected from the group consisting of: ##STR142## 
     
     
       41. The silver halide color photographic material as claimed in claim 1, wherein R 21  in Formula (III) is selected from the group consisting of: ##STR143## 
     
     
       42. The silver halide color photographic material as claimed in claim 1, wherein R 22  in Formula (III) is selected from the group consisting of: ##STR144## 
     
     
       43. The silver halide color photographic material as claimed in claim 1, wherein Z 1  in Formula (III) is selected from the group consisting of: ##STR145##